Water-soluble condensation product and its manufacture



re nted M y 7,1940 I I ff I v 2,199,776

it UmrsosrArEs ifP A'lEN'ldOFFlCE"I I Fritz -Becherer, Riehen, nearBasel, Switzerland, 'assignor to the firm J. R. Geigy A. G., Basel,- I

' Switzerland I I r No Drawing. Application May 18, 1938, Serial I v No.208,719. In Switzerland May 24, 1937 Claims. (01. 260-386) Thisinventionrelates to the manufacture of 128 gms. of naphthalene are added266 gm of water-soluble condensation products, that maybebenzaldehyde-Z:4-disulphonic acid and the whole used for variouspurposes in industry. stirred for 4 hours at 3540 C. After this period II It has now been found that valuable condensathe aldehyde reaction canno longer be observed, '5 tion products are obtained of the general for-The product is cooled to 20 C. and 164 gms. ofv 5 111111941, I Hbutyl-o-cresol-:added bit by bit-.- The final con- R densation iscompleted after several hours, and v 0 the product has then becomesoluble in water. 7 e I The action product, a resinous material, which10 I I has separated out is removed from the acid, is -10 I I Idissolved in water, and after neutralisation which may be made withlime, it is freed with steam V from unchanged starting materials. There- (in which I is 1 or 2, R is an unsubstituted or ns solution a be v pat d to dry s r '15 substituted aromatic hydrocarbon residue or hythe fiD t y p p te by Sodium droaromatic hydrocarbon residue containing un-Chloride, filtered and A bllght D E P saturated bonds, R, is the a id asR product is obtained which represents a very satisan aromatic residuecontaining a hydroxyl group factory reserving agent which may also befurther substituted, and z Example wherein the benzene nucleus, whichcarries one or a plurality of sulphonic acid groups, may in 130 PnapIhtha 1ene are fused Y 100 addition contai halogen and nitm u if gms.of glacial acetic ac1d and the melt is st rred aromatic aldehydesulphonic acids or their func into 1100 gms. of concentrated sulphuricacid in tional derivatives are condensed with unsub- Whlch aresuspendeId P stituted or substituted aromatic or condensiblealdehyde5'sulpho'mc acld- Amer Stmmg for 26 hydro-aromatic hydrocarbeither in the several hours at 40-50 0., no further aldehyde molecularratio 1:2 or with hydrocarbon compo- Sulphonic acid observable andnaphthalene nents reduced to the ratio 1:1, and the interis also usedupexcept for traces- 206 0f mediate compounds, which are still capable of'isobutyl Phenol are now added and the Whole 30 reaction are furthercondensed with phenols, or further condensed at the same temperatureuntil 30 their derivatives or substitution products. a test portion isfound '9 form a clear Solution Advantageously, the process is carriedout by Without any sepaliaitloni Water- Furthel: treatcondensing thehydrocarbon in the presence'of ment can b earned out m accordance Wlthone a solvent, a diluting or a condensing medium such f the methods Setforth in Example as sulphuric acid at various concentrations, Example 335 glacial acetic acid, chlorosulphonic acid, or by drochloric acid,ZnClz, with an aldehyde monoi 231 of 27chlorobenzaldehyde'5 su1phomc orpoly-sulphonic acid to the end stage or at least p are added to mlxtureof 274 of until the aldehyde reaction has disappeared, and narybqtylcyclohexene 850 m f then combining the intermediate product with a.sulphunc a of glacml acetm phenol to form the end product: Theconditions and the mlxture S mimtained at 40-590 union of temperatureand time of this reaction may be the aldehyde sulphomc and has pracucauyal.8- varied within wide limits and depend largely on appeared and theProduct h become p i m the condensabmty of the compounds used water. Thewhole is then diluted with a mixture The products may be used for themost varied of W and water the cortdensatmn product 15 45 purposes inindustry In a number of cases they precipitated by means of brme, andafter neutral-- f dried. The condensation product is a represent veryefiective wettin emulsfi in", and 13 dispersing agents and detergeitsFlurghelfmore slightly brown-coloured powder with very distinct some ofthe new com ounds are eminentl suited Wettmg property i as reservingagents for wool in the haYli-wool AS aldehyde 5111131191110 W '1 ordyeing industry e dehyde sulphonic acid, 2.5- or 2.6-benzaldehydedisulphonic acid can be used with equal success;

. instead of naphthalene may be used amyl-naph- To a mixture of 900gms..of concentrated sulthalene, chloronaph h l n p n nt 56 phuric acid,250 gms. of glacial acetic acid and thracene or tetraline.

Example 1 b-(SOxH):

wherein R represents the residue of a member of the group comprisingaromatic and hydroaromatic hydrocarbons containing unsaturated bondscapable of being condensed with benzaldehyde sulphonic acids, and

R represents the residue of a member of the group above described for R.with the addition of a condensible monohydric body of the benzeneseries.

LE, being an integer from 1 to 2, being when neutralised and evaporated,colorless powders of good solubility in water, the aqueous solutions ofwhich possess remarkable capillary properties.

2. Textile assistants, particularly adapted for use as wool reservingagents, being the products of reaction of 1 mol. of abenzaldehyde-sulphonic acid with 1 mol. of naphthalene and 1 mol. of anuclear alkylated condensible phenol of the benzene series, being whenneutralised and evaporated colorless powders of good solubility inwater, the aqueous solutions of which possess remarkable capillaryproperties.

3. A textile assistant, particularly adapted for use as a Wool reservingagent, being the product of reaction of 1 mol. ofbenzaldehyde-o-sulphonic acid with 1 mol. of naphthalene and 1 mol. ofdiisobutyl-phenol, being when neutralised with an alkali and evaporated,a colorless powder of good solubility in water, the aqueous solutions orwhich possess remarkable capillary properties.

4. A textile assistant, particularly adapted for use as a Wool reservingagent, being the product of reaction of 1 mol. of2-chlorobenzaldehyde-5- sulphonic acid with 1 mol. of naphthalene and 1mol. of di-isobutyl-phenol, being when neutralised with an alkali andevaporated, a colorless powder of good solubility in water, the aqueoussolutions of which possess remarkable capillary properties.

5. A textile assistant, particularly adapted for use as a wool reservingagent, being the product of reaction of 1 mol. ofbenzaldehyde-o-sulphonic acid with 1 mol. of naphthalene and 1 mol. oftertiary butyl-phenol, being when neutralised with an alkali andevaporated, a colorless powder of good solubility in water, the aqueoussolutions of which possess remarkable capillary properties.

FRITZ BECI-EERER.

